My Second Try At Roll 20. Still can't wrap my head around it

Some years ago I actually ran a roll20 game called Nazis & Nightmares.  Third Reich gets a hold of black magic, and starts using it to win the war.  Only the courage of your valiant commandos can... yaddah, yaddah.  You know the drill. Anyway, though we got it yo work, sort of, we eventually abandoned it, because the programming was so whonky, or at least not particularly transparent.  I'm back for another try, but it still seems that so many things are much more difficult than they need to be, and so many obviously necessary things that you just can't do. For instance. The system I'm running is called Swordsmen & Skeletons.  I am the writer and copyright holder.  It is a version of the original rules that fits on a single sheet of paper, and so is a pretty good pick for an online campaign. So why can't I upload the pdf anyplace in my game? I'm willing to admit that I might be a drooling idiot, and unable to figure out how to do this, but it seems like exactly the sort of thing you would need to be able to do in just about any rpg. Sure, you couldn't upload the 5e Player's Handbook, but any game system should allow the GM to upload documents like home brewed adventure modules and house rules.   Or is it possible that this can be done, but it is either buried in some weird, esoteric part of the program, or I'm just too much of a lunkhead to figure it out? One thing. PLEASE DON'T POINT ME TO THE BEGINNER'S TUTORIAL.  I went through the whole thing once before, and it wasn't particularly elucidating. For now, just allow that I'm an idiot, and tell me how I can do this one thing. P.S. The ability to upload a single jpg or png file is not helpful here.  I'd need this to be something that would not have to be replaced the next time I needed to upload such a file. Or is this a matter of bandwidth? Would everything have to be stored someplace else on the web, and just linked here?

You cannot upload an entire PDF to Roll20 for viewing. If you want to host a PDF, there are many other websites or applications that can do so. For example, you could link the PDF on a Discord Server, or  send a link to your players through Firefox Send or Google Drive.  You can somewhat emulate uploading a PDF to Roll20 if you like, by exporting the PDF as an image. To do this, open the PDF on your computer and save it as a JPEG. Then, you can create a new handout and use that image for the handout. You could create several images if you have several pages. Still though, Roll20 isn't the ideal platform for sharing PDFs, as there are countless ways you could get the rulebook to your players otherwise.

There are three ways you can do this currently: You can drag a PDF from your computer into the image part of a handout and upload a page from it. It will come in as an image.  You can create a handout, copy the text from your PDF into the text of the handout.  You can provide a link to players to a site to get the pdf.  2 is the best way to handle this fir Roll20. Handouts are the native documentation format for the system. This allows them to be accessed by the game snd the browser appropriately, lets screen readers read them, let's local Browser's settings for font size, font choice, contestant, etc. take effect. Additionally, a handout can be managed in the user interface of Roll20 by the players. Minimized by double clicking the header, resized to fit their screen, layered with characters sheets, and so on.  PDFs are designed to look nice when printed. They are not the native format of web pages. Uploading an image of a page is intended to allow easily including charts or images or important diagrams to be easily included.  If you absolutely need your players to have the document as a PDF, providing them a link will let them load it in a local native PDF viewer. 

And if it is in text handout(s), the GM can search for words within it from the search box in the right-hand pane. And hopefully one day players will also be able to search their handouts.